N-(3-hydroxy-4-pyrrolidin-1-ylmethylphenyl)acetamide | 133914-75-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(3-hydroxy-4-pyrrolidin-1-ylmethylphenyl)acetamide
• 英文别名: N-[3-hydroxy-4-(pyrrolidin-1-ylmethyl)phenyl]acetamide；5-acetamido-2-(pyrrolidinomethyl)phenol
• CAS: 133914-75-7
• 化学式: C₁₃H₁₈N₂O₂
• 分子量: 234.298
• InChiKey: HYXOIQHNIKRNRD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  52.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(3-hydroxy-4-pyrrolidin-1-ylmethylphenyl)acetamide 在 盐酸 、 水 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 5-(7'-chloroquinolin-4'-ylamino)-2-(pyrrolidin-1''-ylmethyl)phenol
  参考文献：
  名称：

  [EN] 7-CHLORO-QUINOLIN-4-AMINE COMPOUNDS AND USES THEREOF FOR THE PREVENTION OR TREATMENT OF DISEASES INVOLVING FORMATION OF AMYLOID PLAQUES AND/OR WHERE A DYSFUNCTION OF THE APP METABOLISM OCCURS
  [FR] COMPOSÉS DE 7-CHLORO-QUINOLIN-4-AMINE ET LEURS UTILISATIONS POUR PRÉVENIR OU TRAITER LES MALADIES IMPLIQUANT LA FORMATION DE PLAQUES AMYLOÏDES ET/OU UN DYSFONCTIONNEMENT DU MÉTABOLISME DE L'APP

  摘要：

  本发明涉及具有以下式（I）的化合物，用于预防和/或治疗涉及淀粉样斑块形成和/或APP代谢功能障碍的疾病。

  公开号：

  WO2011073322A1
• 作为产物：
  描述：

  四氢吡咯 、 聚合甲醛 、 N-(3-羟基苯基)乙酰胺 以 乙醇 、 水 为溶剂， 以80%的产率得到N-(3-hydroxy-4-pyrrolidin-1-ylmethylphenyl)acetamide
  参考文献：
  名称：

  [EN] 7-CHLORO-QUINOLIN-4-AMINE COMPOUNDS AND USES THEREOF FOR THE PREVENTION OR TREATMENT OF DISEASES INVOLVING FORMATION OF AMYLOID PLAQUES AND/OR WHERE A DYSFUNCTION OF THE APP METABOLISM OCCURS
  [FR] COMPOSÉS DE 7-CHLORO-QUINOLIN-4-AMINE ET LEURS UTILISATIONS POUR PRÉVENIR OU TRAITER LES MALADIES IMPLIQUANT LA FORMATION DE PLAQUES AMYLOÏDES ET/OU UN DYSFONCTIONNEMENT DU MÉTABOLISME DE L'APP

  摘要：

  本发明涉及具有以下式（I）的化合物，用于预防和/或治疗涉及淀粉样斑块形成和/或APP代谢功能障碍的疾病。

  公开号：

  WO2011073322A1

文献信息

• NEW HETEROCYCLE COMPOUNDS AND USES THEREOF FOR THE PREVENTION OR TREATMENT OF DISEASES INVOLVING FORMATION OF AMYLOID PLAQUES AND/OR WHERE A DYSFUNCTION OF THE APP METABOLISM OCCURS
  申请人：Delacourte Andre

  公开号：US20120283256A1

  公开（公告）日：2012-11-08

  The present invention relates to compounds having the following Formula (I) for use in the prevention and/or the treatment of diseases involving formation of amyloid plaques and/or where a dysfunction of the APP metabolism occurs.

  本发明涉及具有以下式（I）的化合物，用于预防和/或治疗涉及淀粉样斑块形成和/或APP代谢功能紊乱的疾病。
• Heterocycle compounds and uses thereof for the prevention or treatment of diseases involving formation of amyloid plaques and/or where a dysfunction of the APP metabolism occurs
  申请人：Delacourte Andre

  公开号：US08680095B2

  公开（公告）日：2014-03-25

  The present invention relates to compounds having the following Formula (I) for use in the prevention and/or the treatment of diseases involving formation of amyloid plaques and/or where a dysfunction of the APP metabolism occurs.

  本发明涉及以下式（I）的化合物，用于预防和/或治疗涉及淀粉样斑块形成和/或APP代谢功能障碍的疾病。
• Dye couplers
  申请人：Bristol-Myers Squibb Company

  公开号：EP0398702A2

  公开（公告）日：1990-11-22

  The present invention concerns the aminophenols (I) as novel couplers wherein R₁ and R₂ may be the same or different and are hydrogen, alkyl and hydroxyalkyl of from 1 to about 6 carbons in the alkyl moiety, or R₁ and R₂ can also form, together with the nitrogen atom to which they are attached, a morpholine, piperidine or pyrrolidine ring, and R₃ and R₄ are hydrogen, alkyl, acyl and hydroxyalkyl having from 1 to about 6 carbons, and oxidative hair dye compositions containing same along with at least one primary dye intermediate in aqueous or hydroalcoholic media.

  本发明涉及作为新型偶联剂的氨基苯酚 (I) 其中，R₁ 和 R₂ 可以相同或不同，并且是氢、烷基和烷基中 1 至 6 个碳原子的羟烷基，或者 R₁ 和 R₂ 也可以与它们所连接的氮原子一起形成吗啉环、哌啶环或吡咯烷环，而 R₃ 和 R₄ 是氢、烷基和羟烷基、R₃和 R₄是氢、烷基、酰基和羟基烷基，具有 1 至 6 个碳原子，以及在水性或水醇介质中含有至少一种主染料中间体的氧化染发组合物。
• Isoquine and Related Amodiaquine Analogues:  A New Generation of Improved 4-Aminoquinoline Antimalarials
  作者：Paul M. O'Neill、Amira Mukhtar、Paul A. Stocks、Laura E. Randle、Stephen Hindley、Stephen A. Ward、Richard C. Storr、Jamie F. Bickley、Ian A. O'Neil、James L. Maggs、Ruth H. Hughes、Peter A. Winstanley、Patrick G. Bray、B. Kevin Park

  DOI：10.1021/jm030796n

  日期：2003.11.1

  Amodiaquine (AQ) (2) is a 4-aminoquinoline antimalarial that can cause adverse side effects including agranulocytosis and liver damage. The observed drug toxicity is believed to involve the formation of an electrophilic metabolite, amodiaquine quinoneimine (AQQI), which can bind to cellular macromolecules and initiate hypersensitivity reactions. We proposed that interchange of the 3' hydroxyl and the 4' Mannich side-chain function of amodiaquine would provide a new series of analogues that cannot form toxic quinoneimine metabolites via cytochrome P450-mediated metabolism. By a simple two-step procedure, 10 isomeric amodiaquine analogues were prepared and subsequently examined against the chloroquine resistant K1 and sensitive HB3 strains of Plasmodium falciparum in vitro. Several analogues displayed potent antimalarial activity against both strains. On the basis of the results of in vitro testing, isoquine (ISQ1 (3a)) (IC50 = 6.01 nM +/- 8.0 versus K1 strain), the direct isomer of amodiaquine, was selected for in vivo antimalarial assessment. The potent in vitro antimalarial activity of isoquine was translated into excellent oral in vivo ED50 activity of 1.6 and 3.7 mg/kg against the P. yoelii NS strain compared to 7.9 and 7.4 mg/kg for amodiaquine. Subsequent metabolism studies in the rat model demonstrated that isoquine does not undergo in vivo bioactivation, as evidenced by the complete lack of glutathione metabolites in bile. In sharp contrast to amodiaquine, isoquine (and Phase I metabolites) undergoes clearance by Phase II glucuronidation. On the basis of these promising initial studies, isoquine (ISQ1 (3a)) represents a new second generation lead worthy of further investigation as a cost-effective and potentially safer alternative to amodiaquine.
• 7-CHLORO-QUINOLIN-4-AMINE COMPOUNDS AND USES THEREOF FOR THE PREVENTION OR TREATMENT OF DISEASES INVOLVING FORMATION OF AMYLOID PLAQUES AND/OR WHERE A DYSFUNCTION OF THE APP METABOLISM OCCURS
  申请人：Institut National de la Santé et de la Recherche Médicale

  公开号：EP2513062A1

  公开（公告）日：2012-10-24